$120 Find Cheap Flights from Caribbean to Chicago - Compare and Save

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Cheap Flights from Caribbean to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Chicago

Fri, Jan 15 - Mon, Jan 18
Frontier Logo
5:02 pm - 9:13 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
18h 11m1 stop Tampa
Frontier Logo
8:25 am - 12:37 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
26h 12m1 stop Fort Lauderdale
$227Frontier
Thu, Dec 3 - Sat, Dec 5
Frontier Logo
6:25 am - 1:56 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 31m1 stop Fort Lauderdale
Frontier Logo
5:24 pm - 2:13 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 49m1 stop Orlando
$227Frontier
Thu, Mar 4 - Tue, Mar 9
American Airlines Logo
6:10 am - 9:50 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 40mnonstop
American Airlines Logo
6:48 pm - 1:25 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 37mnonstop
$257American Airlines
Thu, Jan 14 - Mon, Jan 25
American Airlines Logo
7:03 am - 10:35 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
American Airlines Logo
5:01 pm - 11:39 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 38mnonstop
$257American Airlines
Thu, Dec 3 - Tue, Dec 8
United Airlines Logo
8:25 am - 11:49 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mnonstop
United Airlines Logo
1:30 pm - 10:22 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 52m1 stop Washington, D.C. Dulles Intl
$262United Airlines
Fri, Dec 4 - Mon, Dec 14
United Airlines Logo
4:55 pm - 8:26 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 31mnonstop
United Airlines Logo
10:35 am - 10:22 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 47m1 stop Washington, D.C. Dulles Intl
$262United Airlines
Fri, Dec 4 - Mon, Dec 14
JetBlue Logo
6:38 am - 1:30 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 52m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 1:59 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 00m1 stop Fort Lauderdale
$262JetBlue
Mon, Dec 7 - Sat, Dec 12
Multiple Airlines Logo
10:30 am - 11:33 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
15h 03m1 stop Fort Lauderdale
Multiple Airlines Logo
4:00 pm - 1:07 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 07m1 stop Atlanta Hartsfield-Jackson
$266Multiple Airlines
Fri, Nov 20 - Tue, Jan 5
Multiple Airlines Logo
6:00 am - 3:57 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
11h 57m1 stop Baltimore/Washington
Multiple Airlines Logo
7:00 am - 11:47 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
14h 47m1 stop Fort Lauderdale
$271Multiple Airlines
Tue, Nov 24 - Tue, Dec 1
JetBlue Logo
6:00 am - 1:32 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 32m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 1:59 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 00m1 stop Fort Lauderdale
$283JetBlue
Useful Info

Good to know

Low season

March

Cheapest flight

$120
Best time to beat the crowds but there is an average 36% increase in price.
Flight from San Juan to Chicago Midway Airport

FAQs for booking flights from Caribbean to Chicago

  • How does KAYAK find such low prices on flights from Caribbean to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Caribbean to Chicago

 
Need help choosing which airline to fly with from Caribbean to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4217 reviews
8.6Crew
8.1Boarding
7.4Entertainment
8.0Comfort
7.0Food
Airline reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

2.0 MediocreKevin, Oct 2026
Read more Southwest reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

I had bad experience with United airline. No live rep, they only have AI that respond to customers concern

Flight and crew were great. Need more legroom and do not allow seats to recline.

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

The whole experience at the airport in Istanbul should be made known beforehand. Four passport checks and a huge check-in line as I could not check in online made it a very lengthy and frustrating experience. The flights on Turkish Airlines however were just fine.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

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